Northwest Chicago Vacations from ￥218,942

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The Latest Northwest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
The cleanliness of the hallways in the hotel and on the pier was exceptional. The views of the water and downtown lights were the best and all the eating places on the pier were excellent choices to choose from.

Reviewed on Aug 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Location, staff and accommodations were excellent.

Reviewed on Aug 13, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Food prices parking prices

Reviewed on Aug 13, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Being right on the river with great views made this even better! Close to everything & friendly, helpful staff

Reviewed on Aug 13, 2025

Find the Best Northwest Chicago Vacation Packages

Northwest Chicago Hotel Deals

Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,523 per night from Aug 26 to Aug 27
￥17,523
￥20,148 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (1,202 reviews)
"Rooms were clean however the bathroom was a little tight for a small family of 3. You can tell they renovated recently which is a plus. Would stay here again if needed to."

Reviewed on Aug 11, 2025

Hyatt Regency Schaumburg Chicago
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is ￥19,656 per night from Aug 24 to Aug 25
￥19,656
￥23,074 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,365 reviews)
"My only issue was my room was right next to the elevator and I can hear it running throughout the day when I was trying to take a nap"

Reviewed on Aug 12, 2025

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥26,395 per night from Sep 5 to Sep 6
￥26,395
￥30,985 total
Sep 5 - Sep 6
includes taxes & fees
8.2/10 Very Good! (2,102 reviews)
"Very convenient for early/late flights, room clean, overall quiet, bed was pretty soft/low to the ground, service a little slow."

Reviewed on Aug 12, 2025

Hilton Chicago O'Hare Airport
See all 3,733 properties in Northwest Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Northwest Chicago

Woodfield Mall which includes shopping as well as a small group of people

Woodfield Mall

Browse through over 300 stores, restaurants and specialty shops at Schaumburg’s expansive shopping mall, one of the largest in the United States.

Woodfield Mall
Legoland Discovery Center showing art

LEGOLAND® Discovery Center

See iconic Chicago landmarks made from over a million LEGO® pieces, watch a movie and learn how the bricks are made in the LEGO® factory.

LEGOLAND® Discovery Center

Harper College

Enjoy the collegiate vibe at Harper College during your stay in Palatine. Amble around this quaint area's lakeside or attend a sporting event.

Harper College

What to do in Northwest Chicago

River tour boat in Chicago

Architecture River Tour

￥6,122
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,646
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥5,981
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Northwest Chicago

Frequently asked questions

How much does a Northwest Chicago vacation package cost?
Much less than you might think — from as low as ￥218,942, actually! By bundling hotels, flights and car rentals into your own tailor-made vacation package, your Northwest Chicago escape is only clicks away.
How do I get a cheap travel package to Northwest Chicago?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a Northwest Chicago vacation package and save. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the flexibility to tailor your vacation your way. We offer more than 550 airlines and 1,000,000 hotels in all corners of the globe, so that everyone has an opportunity to travel and fulfill those vacation dreams.
What are the top hotels in Northwest Chicago?
When it comes to properties in Schaumburg, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are two popular options. If you're also visiting West Dundee, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my Northwest Chicago vacation?
Reserving your spot early with Expedia means one less thing to worry about. Many air carriers advertise prices up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, great deals to Northwest Chicago are still known to appear in the weeks leading up to departure.
What does an Expedia Northwest Chicago travel package include?
It depends on what type of escape you have in mind. Northwest Chicago vacation deals can include hotels, flights and car rentals. You can mix and match to create the travel package that suits you. You can also add on activities and experiences after you've booked to land even bigger discounts.
What should I know before booking a Northwest Chicago travel package?
A travel package can be tailored to your budget and is a fantastic way to stretch your dollars further. What you include is totally up to you. Rental cars, hotels and flights — choose any combination that suits your plans.
Can I choose my airline with a Northwest Chicago Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're in control. We have access to more than 550 airline partners all over the world, so you have loads of choice when arranging your Northwest Chicago adventure.
If I'm not able to travel, can I cancel my Northwest Chicago vacation package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Northwest Chicago vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company for older bookings. If life gets in the way of your vacation, take a look at our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.